The reaction of diamines and difunctional acidic materials is well known in the art to produce polyamide polymers. A commercial example of the production of such polymers is the illustrative reaction of hexamethylenediamine adipic acid to produce the polyamide known as NYLON.RTM. 66. The nature of the polyamide product will vary, depending in part on the nature of the acid compound and the amine.
The reaction of a ketobenzoic acid, i.e., benzoylbenzoic acid, and diamines is shown by Hovey et al, U.S. Pat. Nos. 2,149,678 and 2,195,570. The reaction of aromatic dicarboxylic acids and photosensitive diamines is shown by Nakama et al, U.S. Pat. No. 4,595,745. Caldwell et al, U.S. Pat. No. 3,408,334, describe the reaction of dicarboxylic acids and diamines in the presence of a tin compound as catalyst. Reaction of .alpha.,.beta.-unsaturated carboxylic acids and primary and secondary diamines is disclosed by Conciatori, U.S. Pat. No. 3,637,602. The use of a dicarboxylic acid of additional functionality, e.g., 4-oxoheptanedioic acid, in the production of polymers is shown by Ferstandig, U.S. Pat. No. 2,987,502, but the reaction was with a polyhydric alcohol and the product was a polyester. The reaction of this type of acid with diamines is shown by Jacobson, U.S. Pat. No. 2,279,752.
A class of compounds that function in many ways similar to dicarboxylic acids is the class of 1,6-dioxa [4.4] spirodilactones. The simplest member of the class, 1,6-dioxaspiro[4.4]nonane-2,7-dione, is known and has been prepared, among other procedures, by the method of Pariza et al, Synthetic Communications, Vol. 13(3), pp. 243-254 (1983). These spirodilactones have demonstrated utility as curing agents to produce compositions which do not shrink upon curing. This property probably results from opening of the spirodilactone ring system during the curing process, Knowles et al, J. Appl. Polymer Science, Vol. 10(6), pp. 887-889 (1966). It is generally characteristic of the spirodilactone ring system that it tends to produce ring-opened products as further evidenced by the above Pariza et al article and Cowsar et al, U.S. Pat. No. 4,064,086.
There are some processes in which the spiro ring system of a spirodilactone reactant is retained in part or in total. Cowsar et al, "Biodegradable Polyamides Based on 4,4'-Spirobibutyrolactone", ACS Meeting Abstract (Los Angeles, 1988), pages 521-525, describe a terpolymer prepared from reaction of a spirodilactone and diamine in which some units retain a spiro structure and others do not. U.S. Pat. No. 4,889,907 and allowed and Ser. No. 245,618 filed Sept. 16, 1988, describe and claim a process in which spirodilactones react with hydroxy-containing primary amines to produce monomeric substituted spirolactonelactams or spirodilactams. A copending U.S. patent application Ser. No. 314,513, filed Feb. 23, 1989, describes and claims certain monomeric products produced by reaction of two molecules of a primary diamine and one molecule of a spirodilactam precursor selected from ketodicarboxylic acid compounds or spirodilactones.
A copending U.S. patent application Ser. No. 254,432, filed Sept. 16, 1988 describes and claims certain polyamide polymers containing 1,6-diazo [4.4] sirodilactam moieties as well as the process of their production by reaction of primary diamines and a spirodilactam precursor as above defined. Such polymers are linear alternating polymers wherein moieties derived from the diamine alternate with spirodilactam moieties. By conducting this polymerization reaction with a mixture of primary diamines, it is possible to produce a linear alternating polymer wherein the alternate diamine moieties are a random mixture of the diamines in the mixed diamine reactant. It would be of advantage, however, to provide a process for the production of such polyamide polymers wherein moieties derived from a primary diamine alternate with spirodilactam moieties derived from two different primary diamines also alternate within the polymeric chain. Such a polymer is produced through isolation of an intermediate in the polymer production process and subsequent reaction with dissimilar diamine.